Healdsburg Vacation Rentals

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Vacation Rentals in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining
Fridge, microwave, oven, stovetop
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, 278 reviews
"We were so impressed the first time that we stayed here, we had to come back again. The house is beautiful and perfect for two couples. And the view from the deck...amazing!"
Wooded Restful Retreat, with broad scenic views, outdoor dining
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Fridge, microwave, oven, stovetop
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
10.0 out of 10, Exceptional, 263 reviews
"Our favorite place to stay for R&R. Private and peaceful, surrounded by vineyards. Close to town, but away from it all. Love it. Thanks again as always, Wayne and Pauline!"
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Property grounds
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, 148 reviews
"We love staying at this property in Dry Creek! It is so clean and has everything you'd want.. the location is perfect, right in the middle of everything Dry Creek and Healdsburg."
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
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E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
Property grounds
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
8.8 out of 10, Excellent, 3 reviews
"Really nice private area on the property - for the review about the wifi - it worked wonderful - was gone during the day but relaxing and good vibe when I was there. Nice outside area as well."
The price is $149
$187 total
includes taxes & fees
Jun 2 - Jun 3
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
Healdsburg Cottage Walk to the Plaza, Workspace
Property grounds
Healdsburg Cottage Walk to the Plaza, Workspace
10.0 out of 10, Exceptional, 205 reviews
"This cottage was by far one of best we have stayed in. Immaculate, charming, everything we needed. Lovely!"
Healdsburg Cottage Walk to the Plaza, Workspace
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Property grounds
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
9.8 out of 10, Exceptional, 19 reviews
"We loved this property! We did a mini high school reunion with friends from 40 years ago. The house was amazing and did not disappoint at all. We laid by the pool, played cards outside. Close to Healdsburg Square (7 minutes away). This trip was beyond all our expectations and the house was clean and big and the view was amazing. Recommend for a group of 8 or less. We will definitely book again!"
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
Chalk Hill Cottage Close to Wineries
Exterior
Chalk Hill Cottage Close to Wineries
9.8 out of 10, Exceptional, 15 reviews
"Lovely place for a couple to stay. Convenient location - close to many vineyards and the great town of Healdsburg!"
Chalk Hill Cottage Close to Wineries
Newly Refurbished! Nest Cottage at ru's Farm.
Property grounds
Newly Refurbished! Nest Cottage at ru's Farm.
10.0 out of 10, Exceptional, 148 reviews
"We thoroughly loved staying here!!!"
Newly Refurbished! Nest Cottage at ru's Farm.
Riverside Cottage in Healdsburg
Living area
Riverside Cottage in Healdsburg
8.8 out of 10, Excellent, 5 reviews
"We stayed at the Riverside Cottage for 3 weeks and it was so peaceful, relaxing and homey. It was just me and my husband and we enjoyed every minute. The place is only 7 minutes from downtown Healdsburg, but far enough away to feel like you are tucked away in the woods. It was perfect for the two of us."
Riverside Cottage in Healdsburg
B - Wine Country Getaway
Fridge, microwave, oven, stovetop
B - Wine Country Getaway
9.6 out of 10, Exceptional, 10 reviews
"We were looking for a place to stay for a wine weekend, and this place was perfect. Cozy and great location, easy in/out."
B - Wine Country Getaway
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
Fridge, microwave, oven, stovetop
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
10.0 out of 10, Exceptional, 213 reviews
"Lovely property and convenient."
Beautiful Cottage overlooking vineyards. Three minutes from downtown!
Hidden Oasis ~ a Private Luxury Home in Healdsburg
Property grounds
Hidden Oasis ~ a Private Luxury Home in Healdsburg
10.0 out of 10, Exceptional, 11 reviews
"Property was a terrific place to use as a base to explore wine country. Outdoor space is great! Would definitely recommend it."
Hidden Oasis ~ a Private Luxury Home in Healdsburg
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
A heated pool
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
10.0 out of 10, Exceptional, 20 reviews
"Amazing house. Very expensive but worth it if you have a big group and want a nice pool. High end kitchen and comfortable large beds in every room. We had one moderate issue where the fire pit was broken and the host responded quickly and replaced it the next day, good communication. Would rent here again."
Sanctuary on Lytton -- a true Sanctuary in the heart of wine country!
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
Pool | Outdoor pool, a heated pool
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
10.0 out of 10, Exceptional, 133 reviews
"Beautiful central location, comfortable and clean. Just slightly dated."
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
Dry Creek Cottage - Healdsburg
Pool
Dry Creek Cottage - Healdsburg
9.8 out of 10, Exceptional, 131 reviews
"Second time at this property- it’s quiet and relaxing. The pool and hot tub felt amazing after a long day of exploring."
Dry Creek Cottage - Healdsburg
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Fridge, microwave, oven, stovetop
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
10.0 out of 10, Exceptional, 46 reviews
"This was the perfect setting for our mothers/daughters wine trip! We had plenty of room to spread out (8 of us) comfortably. The grounds, landscaping, vineyard are simply spectacular! The house is well equipped with all party essentials like a nice big kitchen, beautiful pool and hot tub and seating. We had great communication before, during and after our stay. We also loved that we felt very safe and private! The location is perfect for all Healdsburg area spots!"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Bella Fattoria-HBG Farm to Table Hideaway
Property grounds
Bella Fattoria-HBG Farm to Table Hideaway
10.0 out of 10, Exceptional, 19 reviews
"We had a wonderful stay at Bella Fattoria, aka Milk Barn. The house was in wonderful shape and slept two couples and a baby with lots of room to spare. The outdoor space is the highlight and we loved the pool, the hot tub, the croquet, and all the other outdoor games and spaces. The house and ground were very clean and nice, and the location was perfect. Only a five minute drive from either Healdsburg or Windsor, and we were able to walk to Merriam winery. We will definitely stay here again."
Bella Fattoria-HBG Farm to Table Hideaway
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
Outdoor pool
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
10.0 out of 10, Exceptional, 15 reviews
"We absolutely LOVED staying here! There were four of us, and there was plenty of room! We loved the grounds - being next to the winery - getting a personal tasting - and just enjoying the living space! Great places to walk around the vineyard, and we were less than 5 minutes away from downtown Healdsburg! It's centrally located, just off the 101. AND, the wine bottle-shaped pool was the icing on the cake!! I would HIGHLY recommend Limerick Lane as a perfect spot to get away with friends or...
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
Property grounds
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
10.0 out of 10, Exceptional, 30 reviews
"Great property with 10 mins from Healdsburg Plaza."
Dog-friendly home on 10 acres w/private hot tub, English garden, patio
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
Golf
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, 157 reviews
"The location is remote and peaceful with great views and minutes from Healdsburg. We would recommend the Wine Country Walking Tour with Greg (amazing!) We also did an exciting self-guided raft trip with Russian River Adventures. The hot tub at Fitch Mtn Lookout was a welcome treat after rafting. The only challenge of FML is, if you are in the top bedroom, it's 2 flights down to the bathroom in the night but the stairs have nice lighting. The hosts are very responsive with any questions you might...
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣‍♀️ Semi-Private Beach🏖Lux Spa
Don't see what you're looking for?
See all available properties in Healdsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Healdsburg Vacation Rental Travel Info

Number of vacation rentals
54
Popular accommodation
Healdsburg private vacation homes
Known landmarks
Armstrong Redwoods State Park, Francis Ford Coppola Winery and Dry Creek Vineyard
International airports
San Francisco, CA (SFO-San Francisco Intl.) and Santa Rosa, CA (STS-Sonoma County)

Other types of properties in Healdsburg you may be interested in

Best Western Dry Creek Inn
Outdoor pool, open 7:00 AM to 10:00 PM, sun loungers
Best Western Dry Creek Inn
3.0 star property
7.8 out of 10, Good, 1,005 reviews
"None"
The price is $159
$185 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Dry Creek Inn
Hotel Trio Healdsburg
Front of property - evening/night
Hotel Trio Healdsburg
3.0 star property
9.4 out of 10, Exceptional, 649 reviews
"Good place!"
The price is $224
$279 total
includes taxes & fees
Jun 9 - Jun 10
Hotel Trio Healdsburg
Montage Healdsburg
2 restaurants, breakfast, lunch, dinner served; Californian cuisine
Montage Healdsburg
5.0 star property
9.4 out of 10, Exceptional, 52 reviews
"Beautiful!"
The price is $837
$1,029 total
includes taxes & fees
Jun 30 - Jul 1
Montage Healdsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Healdsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Healdsburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Healdsburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Healdsburg. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Healdsburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $149 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Healdsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Healdsburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Healdsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near SingleThread Farm at Dry Creek, or you can choose a secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What's the top vacation rental that Healdsburg has to offer?

COZY Bungalow--Dog-Friendly—Perfect for Couples!!! : This vacation home rental outside of Healdsburg is located on the waterfront and offers a selection of books, a Smart TV, and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Healdsburg?

Expedia has 142 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Enjoy the outdoors at Russian River and Austin Creek State Recreation Area, or simply take in cultural attractions like Healdsburg Museum and Raven Performing Arts Theater. Healdsburg Plaza and Mazzocco Winery are other places to visit while you're in town.

What are vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.

Recent reviews of Healdsburg properties
Expedia verified reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

5/5 Excellent
"A perfect stay in wine country! The service was impeccable. The room was sparkling clean and the soaking tub was divine. 10/10"
A verified traveler stayed at The Lodge at Healdsburg, Tapestry Collection by Hilton
Posted 1 day ago
The Lodge at Healdsburg, Tapestry Collection by Hilton